Structure

Physi-Chem Properties

Molecular Weight:  679.99
Volume:  526.746
LogP:  1.036
LogD:  0.862
LogS:  -5.013
# Rotatable Bonds:  7
TPSA:  229.13
# H-Bond Aceptor:  14
# H-Bond Donor:  9
# Rings:  5
# Heavy Atoms:  16

MedChem Properties

QED Drug-Likeness Score:  0.173
Synthetic Accessibility Score:  5.362
Fsp3:  0.25
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.177
MDCK Permeability:  2.2667514713248238e-05
Pgp-inhibitor:  0.994
Pgp-substrate:  0.42
Human Intestinal Absorption (HIA):  0.993
20% Bioavailability (F20%):  0.992
30% Bioavailability (F30%):  0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.041
Plasma Protein Binding (PPB):  98.3836898803711%
Volume Distribution (VD):  0.624
Pgp-substrate:  4.375697135925293%

ADMET: Metabolism

CYP1A2-inhibitor:  0.593
CYP1A2-substrate:  0.915
CYP2C19-inhibitor:  0.669
CYP2C19-substrate:  0.03
CYP2C9-inhibitor:  0.685
CYP2C9-substrate:  0.018
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.051
CYP3A4-inhibitor:  0.836
CYP3A4-substrate:  0.214

ADMET: Excretion

Clearance (CL):  1.343
Half-life (T1/2):  0.755

ADMET: Toxicity

hERG Blockers:  0.216
Human Hepatotoxicity (H-HT):  0.995
Drug-inuced Liver Injury (DILI):  0.971
AMES Toxicity:  0.868
Rat Oral Acute Toxicity:  0.87
Maximum Recommended Daily Dose:  0.85
Skin Sensitization:  0.741
Carcinogencity:  0.695
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.982

Download Data

Data Type Select
General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC185172

Natural Product ID:  NPC185172
Common Name*:   Ceratinadin B
IUPAC Name:   (5S,6R)-N-[2-[2-amino-4-(3,5,8-trihydroxy-4-oxo-1H-quinolin-6-yl)-1H-imidazol-5-yl]ethyl]-7,9-dibromo-6-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,7,9-triene-3-carboxamide
Synonyms:  
Standard InCHIKey:  ZFABPBNMLSLYSF-XUZZJYLKSA-N
Standard InCHI:  InChI=1S/C24H22Br2N6O8/c1-39-20-9(25)5-24(21(37)15(20)26)6-11(32-40-24)22(38)28-3-2-10-16(31-23(27)30-10)8-4-12(33)17-14(18(8)35)19(36)13(34)7-29-17/h4-5,7,21,33-35,37H,2-3,6H2,1H3,(H,28,38)(H,29,36)(H3,27,30,31)/t21-,24+/m0/s1
SMILES:  COC1=C([C@@H]([C@@]2(C=C1Br)CC(=NO2)C(=O)NCCc1c(c2cc(c3c(c2O)c(=O)c(c[nH]3)O)O)[nH]c(=N)[nH]1)O)Br
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1210513
PubChem CID:   49863116
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001253] Quinolines and derivatives
        • [CHEMONTID:0000057] Hydroxyquinolines

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO32681 pseudoceratina sp. Species Pseudoceratinidae Eukaryota n.a. n.a. n.a. PMID[18393464]
NPO32681 pseudoceratina sp. Species Pseudoceratinidae Eukaryota n.a. Okinawan n.a. PMID[20584605]
NPO32681 pseudoceratina sp. Species Pseudoceratinidae Eukaryota n.a. n.a. n.a. PMID[24964362]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MIC = 8.0 ug.mL-1 PMID[475077]
NPT20 Organism Candida albicans Candida albicans MIC = 4.0 ug.mL-1 PMID[475077]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC185172 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.7868 Intermediate Similarity NPC179896
0.6831 Remote Similarity NPC474366
0.6827 Remote Similarity NPC7560
0.6789 Remote Similarity NPC176113
0.6759 Remote Similarity NPC13249
0.6708 Remote Similarity NPC212123
0.6681 Remote Similarity NPC316282
0.668 Remote Similarity NPC122886
0.6667 Remote Similarity NPC218303
0.6654 Remote Similarity NPC285254
0.664 Remote Similarity NPC305542
0.6639 Remote Similarity NPC170333
0.6627 Remote Similarity NPC76478
0.6613 Remote Similarity NPC114468
0.6613 Remote Similarity NPC30749
0.6586 Remote Similarity NPC148391
0.6586 Remote Similarity NPC2905
0.6559 Remote Similarity NPC25961
0.6549 Remote Similarity NPC477394
0.6531 Remote Similarity NPC158551
0.6513 Remote Similarity NPC291173
0.6511 Remote Similarity NPC262725
0.6508 Remote Similarity NPC134702
0.6496 Remote Similarity NPC118189
0.649 Remote Similarity NPC133156
0.6489 Remote Similarity NPC314702
0.648 Remote Similarity NPC217903
0.6475 Remote Similarity NPC1464
0.6464 Remote Similarity NPC151171
0.6448 Remote Similarity NPC477397
0.6443 Remote Similarity NPC182853
0.644 Remote Similarity NPC116178
0.6434 Remote Similarity NPC470480
0.642 Remote Similarity NPC317727
0.6391 Remote Similarity NPC477395
0.6386 Remote Similarity NPC477160
0.6371 Remote Similarity NPC471513
0.6371 Remote Similarity NPC150308
0.6356 Remote Similarity NPC163829
0.6349 Remote Similarity NPC321166
0.6342 Remote Similarity NPC251071
0.6339 Remote Similarity NPC126556
0.6331 Remote Similarity NPC225400
0.6326 Remote Similarity NPC17160
0.6326 Remote Similarity NPC313720
0.6314 Remote Similarity NPC77777
0.6305 Remote Similarity NPC471155
0.6305 Remote Similarity NPC198160
0.6305 Remote Similarity NPC472538
0.6305 Remote Similarity NPC478075
0.6305 Remote Similarity NPC470786
0.6303 Remote Similarity NPC87391
0.6301 Remote Similarity NPC469732
0.6301 Remote Similarity NPC232600
0.6296 Remote Similarity NPC303214
0.629 Remote Similarity NPC87714
0.629 Remote Similarity NPC313112
0.629 Remote Similarity NPC301292
0.629 Remote Similarity NPC14339
0.6289 Remote Similarity NPC219397
0.6289 Remote Similarity NPC222046
0.6285 Remote Similarity NPC268223
0.628 Remote Similarity NPC270241
0.6276 Remote Similarity NPC295531
0.6275 Remote Similarity NPC471197
0.6266 Remote Similarity NPC92803
0.6265 Remote Similarity NPC246140
0.6265 Remote Similarity NPC477161
0.6265 Remote Similarity NPC195787
0.625 Remote Similarity NPC471198
0.625 Remote Similarity NPC18890
0.6245 Remote Similarity NPC132874
0.6245 Remote Similarity NPC265642
0.6245 Remote Similarity NPC470481
0.6245 Remote Similarity NPC473458
0.6245 Remote Similarity NPC470482
0.6245 Remote Similarity NPC138615
0.6245 Remote Similarity NPC218733
0.624 Remote Similarity NPC329830
0.6237 Remote Similarity NPC132385
0.6231 Remote Similarity NPC19175
0.6227 Remote Similarity NPC67401
0.6215 Remote Similarity NPC330683
0.6215 Remote Similarity NPC329567
0.621 Remote Similarity NPC288759
0.6206 Remote Similarity NPC295479
0.6206 Remote Similarity NPC220241
0.6198 Remote Similarity NPC1820
0.6187 Remote Similarity NPC248601
0.6181 Remote Similarity NPC127996
0.6178 Remote Similarity NPC128476
0.6176 Remote Similarity NPC477396
0.6168 Remote Similarity NPC473188
0.6162 Remote Similarity NPC477393
0.6157 Remote Similarity NPC471195
0.6157 Remote Similarity NPC471196
0.6148 Remote Similarity NPC469722
0.6148 Remote Similarity NPC15384
0.6148 Remote Similarity NPC244425
0.6145 Remote Similarity NPC15987
0.6139 Remote Similarity NPC118154
0.6139 Remote Similarity NPC157983
0.6134 Remote Similarity NPC270301
0.6134 Remote Similarity NPC291305
0.6132 Remote Similarity NPC203628
0.6131 Remote Similarity NPC317567
0.6124 Remote Similarity NPC87560
0.6122 Remote Similarity NPC202866
0.6118 Remote Similarity NPC119722
0.6113 Remote Similarity NPC100863
0.6113 Remote Similarity NPC227033
0.6109 Remote Similarity NPC314659
0.6109 Remote Similarity NPC469973
0.6107 Remote Similarity NPC115588
0.6104 Remote Similarity NPC214368
0.6103 Remote Similarity NPC260909
0.61 Remote Similarity NPC475609
0.61 Remote Similarity NPC476250
0.6091 Remote Similarity NPC5630
0.6089 Remote Similarity NPC241263
0.6087 Remote Similarity NPC285192
0.6082 Remote Similarity NPC470485
0.6082 Remote Similarity NPC473187
0.6074 Remote Similarity NPC41501
0.6067 Remote Similarity NPC197335
0.6067 Remote Similarity NPC472163
0.6067 Remote Similarity NPC116096
0.6062 Remote Similarity NPC195120
0.6061 Remote Similarity NPC314987
0.6058 Remote Similarity NPC49184
0.6056 Remote Similarity NPC295548
0.6041 Remote Similarity NPC114039
0.6041 Remote Similarity NPC206109
0.6039 Remote Similarity NPC269449
0.6038 Remote Similarity NPC37957
0.6038 Remote Similarity NPC288110
0.6038 Remote Similarity NPC153923
0.6037 Remote Similarity NPC470784
0.6034 Remote Similarity NPC45048
0.6034 Remote Similarity NPC129624
0.6029 Remote Similarity NPC471536
0.6026 Remote Similarity NPC66490
0.6025 Remote Similarity NPC283207
0.6024 Remote Similarity NPC471336
0.6024 Remote Similarity NPC470746
0.6023 Remote Similarity NPC477828
0.6023 Remote Similarity NPC195636
0.6022 Remote Similarity NPC477549
0.6021 Remote Similarity NPC237901
0.6021 Remote Similarity NPC195788
0.6017 Remote Similarity NPC73280
0.6008 Remote Similarity NPC473815
0.6008 Remote Similarity NPC298449
0.6007 Remote Similarity NPC172222
0.6007 Remote Similarity NPC185031
0.6 Remote Similarity NPC279589
0.6 Remote Similarity NPC244536
0.6 Remote Similarity NPC470483
0.6 Remote Similarity NPC28368
0.6 Remote Similarity NPC313582
0.5993 Remote Similarity NPC181081
0.5992 Remote Similarity NPC41216
0.5992 Remote Similarity NPC198401
0.5985 Remote Similarity NPC179287
0.5985 Remote Similarity NPC470002
0.5985 Remote Similarity NPC208522
0.5985 Remote Similarity NPC470001
0.5984 Remote Similarity NPC16249
0.5984 Remote Similarity NPC234933
0.5984 Remote Similarity NPC112937
0.598 Remote Similarity NPC207620
0.5979 Remote Similarity NPC478006
0.5978 Remote Similarity NPC270515
0.5977 Remote Similarity NPC476651
0.5976 Remote Similarity NPC472330
0.5976 Remote Similarity NPC472329
0.5976 Remote Similarity NPC476662
0.5972 Remote Similarity NPC209981
0.5971 Remote Similarity NPC189079
0.597 Remote Similarity NPC220851
0.5968 Remote Similarity NPC470787
0.5968 Remote Similarity NPC472540
0.5968 Remote Similarity NPC472539
0.5966 Remote Similarity NPC204867
0.5964 Remote Similarity NPC58209
0.5961 Remote Similarity NPC90185
0.5961 Remote Similarity NPC100573
0.5961 Remote Similarity NPC207873
0.5959 Remote Similarity NPC474059
0.5958 Remote Similarity NPC298320
0.5958 Remote Similarity NPC39822
0.5958 Remote Similarity NPC98416
0.5957 Remote Similarity NPC185197
0.5957 Remote Similarity NPC89549
0.5954 Remote Similarity NPC476069
0.5954 Remote Similarity NPC150239
0.5952 Remote Similarity NPC474077
0.5952 Remote Similarity NPC96730
0.595 Remote Similarity NPC97584
0.5946 Remote Similarity NPC189661

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC185172 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.6774 Remote Similarity NPD7292 Approved
0.6667 Remote Similarity NPD3949 Clinical (unspecified phase)
0.6653 Remote Similarity NPD5937 Approved
0.6617 Remote Similarity NPD3986 Discontinued
0.6614 Remote Similarity NPD2899 Discontinued
0.6545 Remote Similarity NPD7302 Phase 3
0.6545 Remote Similarity NPD7300 Phase 3
0.6515 Remote Similarity NPD4668 Phase 2
0.6515 Remote Similarity NPD5194 Approved
0.6515 Remote Similarity NPD5197 Approved
0.6515 Remote Similarity NPD5196 Approved
0.6512 Remote Similarity NPD6199 Discontinued
0.649 Remote Similarity NPD3298 Approved
0.6478 Remote Similarity NPD4022 Approved
0.6478 Remote Similarity NPD3472 Approved
0.6463 Remote Similarity NPD6807 Phase 3
0.644 Remote Similarity NPD4492 Approved
0.644 Remote Similarity NPD4494 Approved
0.6437 Remote Similarity NPD4596 Phase 1
0.6434 Remote Similarity NPD3899 Clinical (unspecified phase)
0.6426 Remote Similarity NPD3372 Discontinued
0.6423 Remote Similarity NPD4456 Clinical (unspecified phase)
0.642 Remote Similarity NPD5608 Approved
0.642 Remote Similarity NPD5609 Approved
0.6411 Remote Similarity NPD4082 Approved
0.6405 Remote Similarity NPD5195 Discontinued
0.6392 Remote Similarity NPD5433 Clinical (unspecified phase)
0.6375 Remote Similarity NPD7301 Phase 3
0.6367 Remote Similarity NPD4946 Phase 2
0.636 Remote Similarity NPD7628 Phase 3
0.636 Remote Similarity NPD7630 Phase 3
0.636 Remote Similarity NPD3893 Discontinued
0.636 Remote Similarity NPD7629 Clinical (unspecified phase)
0.635 Remote Similarity NPD8461 Discontinued
0.6339 Remote Similarity NPD3940 Clinical (unspecified phase)
0.6335 Remote Similarity NPD1945 Phase 1
0.6328 Remote Similarity NPD3783 Clinical (unspecified phase)
0.6322 Remote Similarity NPD4981 Phase 2
0.6316 Remote Similarity NPD4561 Discontinued
0.6314 Remote Similarity NPD7293 Approved
0.631 Remote Similarity NPD3888 Discontinued
0.6307 Remote Similarity NPD5968 Phase 3
0.6286 Remote Similarity NPD3297 Approved
0.6276 Remote Similarity NPD5037 Approved
0.6276 Remote Similarity NPD5038 Approved
0.6275 Remote Similarity NPD6795 Clinical (unspecified phase)
0.6275 Remote Similarity NPD7071 Clinical (unspecified phase)
0.627 Remote Similarity NPD7282 Approved
0.627 Remote Similarity NPD4493 Discontinued
0.626 Remote Similarity NPD4562 Clinical (unspecified phase)
0.6245 Remote Similarity NPD3253 Clinical (unspecified phase)
0.6234 Remote Similarity NPD5036 Approved
0.6226 Remote Similarity NPD5496 Approved
0.6225 Remote Similarity NPD4467 Phase 2
0.6225 Remote Similarity NPD4465 Phase 2
0.6224 Remote Similarity NPD5928 Phase 1
0.622 Remote Similarity NPD4455 Discontinued
0.6215 Remote Similarity NPD2906 Approved
0.6215 Remote Similarity NPD2907 Approved
0.619 Remote Similarity NPD3592 Approved
0.619 Remote Similarity NPD3591 Approved
0.6183 Remote Similarity NPD8059 Phase 3
0.6183 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6179 Remote Similarity NPD5856 Discontinued
0.6174 Remote Similarity NPD3442 Approved
0.6174 Remote Similarity NPD3441 Approved
0.6166 Remote Similarity NPD5860 Discontinued
0.616 Remote Similarity NPD1294 Discontinued
0.6159 Remote Similarity NPD8492 Approved
0.6157 Remote Similarity NPD6836 Approved
0.6145 Remote Similarity NPD7186 Phase 3
0.6145 Remote Similarity NPD956 Clinical (unspecified phase)
0.6142 Remote Similarity NPD683 Approved
0.6139 Remote Similarity NPD3437 Discontinued
0.6138 Remote Similarity NPD4979 Clinical (unspecified phase)
0.6134 Remote Similarity NPD5027 Approved
0.6134 Remote Similarity NPD5029 Approved
0.6134 Remote Similarity NPD5031 Approved
0.6132 Remote Similarity NPD5042 Phase 1
0.6131 Remote Similarity NPD8367 Approved
0.6129 Remote Similarity NPD2339 Phase 3
0.612 Remote Similarity NPD6480 Clinical (unspecified phase)
0.6113 Remote Similarity NPD8067 Phase 3
0.6109 Remote Similarity NPD5028 Approved
0.6109 Remote Similarity NPD4954 Approved
0.6109 Remote Similarity NPD4955 Approved
0.6109 Remote Similarity NPD36 Approved
0.6109 Remote Similarity NPD5034 Approved
0.6109 Remote Similarity NPD5026 Approved
0.6105 Remote Similarity NPD7551 Clinical (unspecified phase)
0.6105 Remote Similarity NPD7550 Clinical (unspecified phase)
0.6103 Remote Similarity NPD8459 Approved
0.6103 Remote Similarity NPD8460 Approved
0.608 Remote Similarity NPD3106 Clinical (unspecified phase)
0.6077 Remote Similarity NPD7858 Clinical (unspecified phase)
0.6074 Remote Similarity NPD7560 Approved
0.6074 Remote Similarity NPD4515 Suspended
0.6073 Remote Similarity NPD4605 Approved
0.6073 Remote Similarity NPD4604 Approved
0.6069 Remote Similarity NPD3912 Discontinued
0.6067 Remote Similarity NPD5030 Phase 2
0.6067 Remote Similarity NPD7922 Phase 1
0.6061 Remote Similarity NPD8469 Approved
0.6056 Remote Similarity NPD7205 Discontinued
0.6056 Remote Similarity NPD7597 Clinical (unspecified phase)
0.6046 Remote Similarity NPD8357 Approved
0.6039 Remote Similarity NPD4997 Clinical (unspecified phase)
0.6037 Remote Similarity NPD7677 Discontinued
0.6033 Remote Similarity NPD3153 Approved
0.6033 Remote Similarity NPD3154 Approved
0.6032 Remote Similarity NPD3964 Approved
0.603 Remote Similarity NPD5151 Clinical (unspecified phase)
0.6021 Remote Similarity NPD8466 Approved
0.6021 Remote Similarity NPD8465 Approved
0.6021 Remote Similarity NPD8429 Approved
0.6021 Remote Similarity NPD8428 Approved
0.6021 Remote Similarity NPD8467 Approved
0.6021 Remote Similarity NPD8427 Approved
0.6016 Remote Similarity NPD4206 Approved
0.6016 Remote Similarity NPD8163 Clinical (unspecified phase)
0.6016 Remote Similarity NPD8162 Phase 2
0.6008 Remote Similarity NPD6161 Approved
0.6008 Remote Similarity NPD6162 Approved
0.6008 Remote Similarity NPD3863 Clinical (unspecified phase)
0.6007 Remote Similarity NPD6456 Discontinued
0.6007 Remote Similarity NPD4373 Phase 2
0.6 Remote Similarity NPD4086 Phase 1
0.6 Remote Similarity NPD6805 Discontinued
0.5992 Remote Similarity NPD6796 Discontinued
0.5992 Remote Similarity NPD6557 Phase 2
0.5985 Remote Similarity NPD6744 Clinical (unspecified phase)
0.5985 Remote Similarity NPD8149 Discontinued
0.5984 Remote Similarity NPD6973 Clinical (unspecified phase)
0.5984 Remote Similarity NPD7584 Approved
0.5977 Remote Similarity NPD7654 Discontinued
0.5977 Remote Similarity NPD5645 Phase 3
0.597 Remote Similarity NPD7031 Phase 1
0.5968 Remote Similarity NPD6644 Discontinued
0.5968 Remote Similarity NPD5102 Clinical (unspecified phase)
0.5959 Remote Similarity NPD4259 Approved
0.5959 Remote Similarity NPD4258 Approved
0.5952 Remote Similarity NPD4386 Approved
0.5952 Remote Similarity NPD4387 Approved
0.5951 Remote Similarity NPD4539 Phase 1
0.595 Remote Similarity NPD5532 Phase 2
0.5948 Remote Similarity NPD6625 Approved
0.5947 Remote Similarity NPD7279 Phase 2
0.5947 Remote Similarity NPD7278 Phase 2
0.5943 Remote Similarity NPD8091 Phase 3
0.5939 Remote Similarity NPD8425 Approved
0.5939 Remote Similarity NPD8426 Approved
0.5938 Remote Similarity NPD5594 Approved
0.5938 Remote Similarity NPD5593 Approved
0.5934 Remote Similarity NPD5637 Discontinued
0.5933 Remote Similarity NPD7552 Discontinued
0.5932 Remote Similarity NPD8155 Clinical (unspecified phase)
0.593 Remote Similarity NPD7225 Discontinued
0.5929 Remote Similarity NPD3802 Phase 3
0.5923 Remote Similarity NPD8363 Approved
0.5923 Remote Similarity NPD5561 Approved
0.5923 Remote Similarity NPD8364 Approved
0.5923 Remote Similarity NPD5562 Approved
0.5913 Remote Similarity NPD7566 Clinical (unspecified phase)
0.5911 Remote Similarity NPD3633 Approved
0.5911 Remote Similarity NPD3634 Approved
0.5907 Remote Similarity NPD4356 Discontinued
0.5896 Remote Similarity NPD4952 Phase 3
0.5896 Remote Similarity NPD6874 Approved
0.5882 Remote Similarity NPD7048 Phase 3
0.5882 Remote Similarity NPD8365 Clinical (unspecified phase)
0.5876 Remote Similarity NPD6790 Phase 1
0.5873 Remote Similarity NPD6612 Phase 2
0.5869 Remote Similarity NPD7605 Discovery
0.5855 Remote Similarity NPD7022 Phase 2
0.5849 Remote Similarity NPD6160 Clinical (unspecified phase)
0.5849 Remote Similarity NPD8311 Discontinued
0.584 Remote Similarity NPD2215 Approved
0.584 Remote Similarity NPD2216 Approved
0.5839 Remote Similarity NPD4894 Discontinued
0.5836 Remote Similarity NPD7589 Clinical (unspecified phase)
0.5836 Remote Similarity NPD6252 Clinical (unspecified phase)
0.5836 Remote Similarity NPD5022 Discontinued
0.583 Remote Similarity NPD2845 Phase 2
0.583 Remote Similarity NPD2843 Phase 2
0.583 Remote Similarity NPD7617 Discontinued
0.5824 Remote Similarity NPD7559 Phase 2
0.5823 Remote Similarity NPD3631 Phase 3
0.5817 Remote Similarity NPD3828 Approved
0.5813 Remote Similarity NPD2942 Phase 2
0.5813 Remote Similarity NPD4951 Discontinued
0.581 Remote Similarity NPD7255 Clinical (unspecified phase)
0.5809 Remote Similarity NPD3793 Phase 3
0.5798 Remote Similarity NPD6518 Discontinued
0.5798 Remote Similarity NPD7263 Phase 2
0.5798 Remote Similarity NPD5143 Clinical (unspecified phase)
0.5794 Remote Similarity NPD4974 Approved
0.5794 Remote Similarity NPD4975 Approved
0.5792 Remote Similarity NPD3803 Clinical (unspecified phase)
0.5789 Remote Similarity NPD6608 Clinical (unspecified phase)
0.5789 Remote Similarity NPD6745 Discontinued

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data